


Kinktober 8

by YlvaUllsdotter



Series: Kinktober 2019 [9]
Category: Supernatural
Genre: BDSM, Bondage, Bottom Dean Winchester, CBT, Cock & Ball Torture, F/M, Femdom, Impact Play, Kinktober 2019, NSFW, Nipple Play, Sadism, Sex, Smut, Sub Dean, Sub!Dean, Submissive Dean Winchester, Unprotected Sex, Wartenberg Wheel, Woman on Top, acousticophilia, clothespins, don't do this kids, pain play, pinwheel
Language: English
Status: Completed
Published: 2019-10-08
Updated: 2019-10-08
Packaged: 2020-11-27 22:31:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20955974
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: Dean asks her to go all out, assuring her that he can take it.





	Kinktober 8

**Author's Note:**

> Day 8 of Kinktober with prompt Sadism. I apologize for nothing.

She had asked him so many times if he was ok with it that he had finally told her to just do it already. _ ‘You asked for it’ _, she had told him and proceeded to make sure the Bunker would be empty for 24 hours, even enlisting Sam to help. Now she found herself walking through the empty hallways, the click of her heels echoing off the tiled walls. Everything was in place. She had told Dean to wait for her in the dungeon, naked and kneeling. She had even used pictures to show him the position she expected him in. 

Idly tapping the riding crop against her leg in time with her steps, she went over everything in her mind again. The toys she had prepared to use on Dean. The order in which she would use them on him. The sounds he would make when she did. She felt a shiver go through her at the thought and smiled to herself.

The door to room 7B was ajar. When she opened it, she had a clear view of the dungeon behind the shelves. Dean knelt on the floor in the position she had told him to assume, naked, his skin glowing in the light of the lamp directly above him. She had assembled her bondage table in the middle of the devil’s trap, and Dean was kneeling directly in front of it, at the outer circle of the trap, perfectly framed by the shelves that formed the doorway to the dungeon. The image before her made her wish she had brought her phone to take pictures. 

She went through the door and closed it behind her. There was no way Dean could possibly have failed to hear her coming, yet he remained kneeling with his head straight, eyes on the floor in front of him. The shelves full of boxes and papers, as well as the different surface, concrete instead of tiles, muffled the sound of her heels on the floor. Still, when she approached Dean she could see his reaction in the tense way he held his back and shoulders, and the way his eyelashes fluttered. She stopped directly in front of him, taking a moment to drink in the sight of him. 

Tapping the leather end of the riding crop lightly under his chin, she prompted him to look up at her, finally allowing him to take in her appearance. She was wearing the new leather harness that had arrived only the day before, with one small adjustment. She wore her best pair of black satin panties, denying him the sight of her pussy. Dean took her in, his eyes traveling up her body until they met hers.

“I’m not going to ask you if you’re sure, Dean. You’ve asked me to do this. This is your last chance to back out. I’ll give you ten seconds to say no. After that, you’re at my mercy, with no way out. Do you understand?”

Dean nodded, never breaking eye contact. She waited the ten seconds she had given him, then nodded and walked off to the side, where she had laid out the things she planned to use on him. 

“Lay on the table, Dean, on your back,” she instructed, her back to him.

Her fingers wandered over the items absentmindedly, her mind on the sound of him getting into position, the sound of his skin against the worn black leather of the bondage table. When he stilled, she turned back and walked up to the side of the table, looking him over.

His eyes were still on her, wondering what was coming. The solid frame of his body filled the surface of the table, a canvas for her to work on. Keeping her face still, she made quick work of the restraints, buckling straps that held him down at wrists, ankles, elbows, knees, chest, and head. She watched his muscles tense when he tested the restraints, then relax when he found himself quite securely bound, unable to move more than an inch in any direction. By the time his eyes wandered back to her, she had already turned away, going to grab the first tool to use.

She quickly returned, what looked like a long shoelace in her hands. Moving his limp cock aside, she wrapped the cord around his balls, stretching and separating them. She secured the ends with a neat bow in the front. Before moving away again, she dragged her nails across the taut skin, scraping lightly and making his skin erupt in goosebumps. It was something she was fond of doing, but what should have been a familiar sensation was suddenly heightened by the bondage, sending jolts of pleasure directly to his cock. The hitch in his breath brought a pleased smile to her lips. 

That smile stayed with Dean when she turned away, sending a warm feeling through him that he could not quite place. Before he had time to analyze it, she was back, this time with a handful of wooden clothespins. He remembered when she got them, remembered asking her about it since they never used clothespins to hang their laundry. She had smirked at him and said nothing, leaving him to wonder. She deposited them in a pile on his abdomen, picking a single one back up. Her free hand held his cock in place while she carefully placed the clothespin just below the tip. He frowned at the feeling. It was not exactly painful, not considering what he had been through, but it was just this side of uncomfortable. She gave him no time to analyze though, proceeding to attach five more pins along the underside of his cock, making it look a bit like he had been attacked by a porcupine. The pins pulled the skin of his cock tight, leaving it oddly sensitive. It was a different kind of sensitive, not like after an orgasm, more like the sensation of his bound balls. It was not unpleasant. Yet.

She flashed him another smile, moving up the table to pinch and play with his nipples. Dean let out a soft sound of pleasure at the feeling. His next sound was a hiss of sharp breath sucked in through clenched teeth when she attached a clothespin to the nipple she had been playing with. The sting of the pin was quickly offset by her fingers on his other nipple, teasing it with light touches. He could see what was coming though and found it difficult to relax into her touch. Sure enough, she attached the pin to his other nipple. Even though he was expecting it, the feeling still made him hiss softly with discomfort.

He had some time to adjust to the feeling while she fetched the next tool. The initial sting quickly settled into a dull discomfort. It was easy enough to ignore. Dean’s eyes widened at the sight of the pinwheel in her hand when she came back into his line of sight. She watched him closely, with an almost expectant look in her eyes. He pressed his lips together, refusing to speak up. He had asked for this. He would not complain. Her pleased smile when he remained silent was reward enough, sending that warm feeling through him again. He recognized it this time. It was the feeling of pleasure from pleasing her.

Before he could dwell on that, he felt the wheel roll over the taut skin of his balls. It felt like a series of shallow pricks from the tip of a blade or a thick needle. It was kind of nice, he decided. 

She watched his face when she rolled the pinwheel across his balls, one at a time. His continued silence was not what she wanted. She wanted to draw sounds from him, and apparently what she had done so far was not enough. She had tried to go slow, considering Dean’s past experiences, but now she could see that would not cut it. She had to step up her game.

Using one of the middle pins on his cock, she pulled it away from his body, rolling the pinwheel up his shaft, pressing it a little harder into his flesh. It drew another hissed breath from Dean, but no more. A little frustrated, she returned the pinwheel to the table, grabbing the riding crop again.

The leather tip of the crop coming down on Dean’s balls finally drew a louder sound from him. He let out a short, sharp cry. She suspected it was more surprise than pain, but it was a start. She tapped the crop against his balls, alternating between them, and occasionally dropping a blow on the tip of his cock. After a few moments of this, Dean started to pant, letting out little groans of pain that shot straight to her core. Yes, this was exactly what she wanted.

Pausing, she reached up and pulled one of the pins off his nipple. The blood surging back into the area made Dean grunt from the sudden pain. She immediately followed that sensation with the crop; quick, sharp taps directly to the nipple, making him try to squirm away. Keeping up the taps with the crop, she reached across him and pulled the other pin off. Dean’s body tried to curl in on itself, to protect itself from the pain. He gasped breaths that became moans of pain when she rubbed her fingers over the sensitive nub, pinching and twisting it. 

Each groan of pain, each gasped breath, sent bolts of pleasure straight to her core. She needed more. Moving back down, she used the crop to slap the clothespins there, harder and harder, until they came off, one by one. Each one slipping off caused Dean to cry out, his muscles tensing in response to the pain. By the time only one was left, he was trembling in his bonds, his body covered in sweat, his whimpering gasps sounding almost like sobs. His eyes were clenched tightly shut, head pressed back against the padded table. 

“Dean,” she said sharply, to get his attention. “Look at me, Dean,” she ordered.

Dean’s eyes shot open and flickered around the room before settling on her. The look of desperation and pain in them was delicious. She glanced at the single clothespin still attached to Dean’s cock by a sliver of skin.

“Don’t close your eyes, Dean. Keep looking at me,” she instructed.

Giving the last pin a firm tap, dislodging it, she watched Dean’s eyes fill with tears, his lips parted around quick shallow gasps, a single breathy sob escaping. She shivered with pleasure. 

“Such a good boy, Dean,” she praised him, even while she kept delivering quick sharp taps to his cock and balls.

She could see the jumble of emotions in his eyes, clear as day. The pain, mixed with determination, and pride. Even if he had had a way out, she doubted he would have used it. He wanted to please her, whatever that would take. Another shiver went through her at the thought.

She moved away from his cock and balls, tapping the riding crop against his inner thighs, one at a time, painting the pale skin there a warm pink. His legs twitched in the restraints, wanting to pull away from the relentless pain, but unable to. She never stopped. The blows rained down, unstoppable, inexorable, inescapable. She experimented with different places on his body, testing which places would draw what sounds from his lips until she was able to play him like an instrument. She was a virtuoso and his sounds of pain were the masterpiece she created.

She lost track of time, using the crop, the cane, the pinwheel, the clothespins, even her hands, to paint his body in the marks of pain. Each sound he made wound her tighter, her pussy throbbing with the need to feel him inside her. Finally, her need for him overtook her need to hear him cry in pain. She dropped the cane on the table and rid herself of her panties; they were ruined now anyway. 

Stroking his cock caused him yet another new type of pain. She licked her lips at the sight of him growing hard in her hand, in spite of the pain it was causing him. Her mind swam with images of what she might do to him some other time. Climbing onto the table, she straddled his legs, one hand stroking his cock, the other alternating between caressing his balls, and raking her nails over the stretched skin. 

When she sank down on him, feeling his cock fill and stretch her so deliciously, their simultaneous cries of pleasure mingled in the cool air of the dungeon. She rode him slowly at first, savoring the feeling of his cock sliding easily into and out of her. Her nails raked down his chest, crossing welts, causing Dean to hiss in pain. Bound as he was, he was unable to even thrust, completely at her mercy. His eyes on hers held a world of desperation, not only to come but to please her. The leftover tears shimmered at the corners of his eyes, wet tracks showing where they had spilled over and run down his temples and into his hair. His lips, parted on gasping breaths, were chapped and dry from the panting. Even that small detail stoked the fire in her body. 

She rode him faster, leaning back to brace her hands on his muscled thighs, watching him. His eyes were seemingly glued to her face, not even glancing down to appreciate the sight of her breasts bouncing with her movements. It was something he usually enjoyed a lot, so it said something about how lost he was in the moment that even that did not pull his attention.

Shifting forward again, she noticed his hands, tightly clenched into fists. Another sign of his desperation. She needed to come now. Bracing her hands on his chest, she rode him hard and fast, finding just the right angle for his cock to hit the spot inside her with each thrust. She slipped one hand between them, finding her clit and rubbing it in tight circles, chasing her high.

With a cry, she tensed on top of him, her thighs gripping his body tightly while she shook with her release. Finally, she collapsed on top of him, panting hard. 

“You ok?” Dean’s breathed words brought her out of her post-coital euphoria. 

She chuckled, sliding off him. Back on her own feet on the floor, she caressed his face, smiling warmly.

“You’re unreal, Dean. I just spent all this time hurting you, making you cry with pain, and you’re asking me if I’m ok?” She shook her head, finding it hard to believe.

Dean blushed but stayed silent. She smiled to herself while she walked around the bondage table, undoing all the straps. When he was free, she helped him sit up and handed him a water bottle. He emptied it in seconds, and she took the empty bottle and tossed it in the trash. He had to lean on her when he got off the table, too unsteady to walk on his own. She helped him to their room, got him settled in bed and tucked in, then snuggled in next to him.

“Thank you, Dean,” she said softly, looking down at him.

“Anything for you,” he whispered hoarsely.

Resting her head on his chest, she listened to his breathing become slower and more even when he slipped into sleep.


End file.
